I'd want to keep my checking account in ledger and real world matching. So either use a virtual account to indicate that some money, while existing in checking, is actually allocated to something else (this is a budget, basically). You can also create asset accounts for what people owe you. Once they pay you you move it from what they owe you to your checking account. For this one, you might have a couple transactions like:

  2018/06/01 Roommate owes me
      Assets:Accounts Receivable       100.00 USD
      Income:Roommate
  2018/06/06 Roommate paid me
      Assets:Checking                  100.00 USD
      Assets:Accounts Receivable

You can drill down another level to add who owes you the money, or perhaps tag it.

The end result is that your checking account is always accurate. Then, as maxerickson says, use virtual accounts to handle mark where the needs to go next or what it's intended for. Also examine ledger's budgeting capabilities for this.

https://www.ledger-cli.org/3.0/doc/ledger3.html#Effective-Da...